Structure and absolute configuration of pyrophen, a novel pryrone derivative of L-phenylalanine from Aspergillus niger.
Pyrophen, a novel 4-methoxy-2-pyrone derivative of L-phenylalanine isolated from cultures of Aspergillus niger, crystallizes in the orthorhombic space group P2(1)2(1)2(1), with a = 8.918(1), b = 9.199(3), and c = 18.092(4) A. The structure was solved by direct methods and the absolute configuration assigned by the Bijvoet method. Refinement gave R = 0.045 and S = 1.78 for 1677 reflections with I greater than 3 sigma (I). Though numerous other pyrone natural products are known, including other products of A. niger, this is the first report of an amino acid-pyrone derivative.
Barnes
C L
CL
Department of Chemistry, University of Puerto Rico, Rio Piedras.
Steiner
J R
JR
Torres
E
E
Pacheco
R
R
Marquez
H
H
D001234:Aspergillus niger / Q000032:analysis; D008968:Molecular Conformation; D015394:Molecular Structure; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry; D011753:Pyrones / Q000737:chemistry*; D014961:X-Ray Diffraction
D011753:Pyrones; C067225:pyrophen; D010649:Phenylalanine